Epichlorohydrin → 2-[(3-Methylbutoxy)methyl]oxirane

Temperature

90 °C

3-Methylbutanol (158 g, 1.78 mol), aluminum triisopropoxide (3.61 g, 17.7 mmol) and p-phenolsulfonic acid (9.40 g, 54 mmol) were charged into a 1-liter reaction vessel and the whole was heated to 90° C. with stirring. After an additional. 1 hour of stirring under reduced pressure (266 hPa). The vessel was heated to 100° C. and epichlorohydrin (170 g, 1.78 mol) was added dropwise thereto over a period of 30 minutes, followed by an additional 3 hours of stirring. The reaction mixture was kept at a 50° C. and 50% sodium hydroxide aqueous solution (285 g, 3.56 mol) was added dropwise thereto over a period of 1 hour. After an additional 3 hours of stirring, 400 ml of water was added to the mixture and the mixture was allowed to separate into layers. After removal of the water layer, 100 ml of toluene was added to the oil layer and the resulting solution was washed with 300 ml of 5% brine three times and concentrated to obtain a crude reaction product (218 g). Distillation of the product gave 3-methylbutyl glycidyl ether (150 g) (bp: 63–64° C./5 hPa, yield 98%).

1. stirring1 hour of stirring under reduced pressure (266 hPa)
2. temperatureThe vessel was heated to 100° C.
3. waitfollowed by an additional 3 hours
4. stirringof stirring
5. customwas kept at a 50° C.
6. waitover a period of 1 hour
7. stirringAfter an additional 3 hours of stirring
8. customto separate into layers
9. customAfter removal of the water layer, 100 ml of toluene
10. additionwas added to the oil layer
11. washthe resulting solution was washed with 300 ml of 5% brine three times
12. concentrationconcentrated
13. customto obtain a crude
14. distillationDistillation of the product

ORD record

ord-eb14a1bebd5143518523294f5d24fa33

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196052B2